I= CHEMICAL INVESTIGATION OF THE METABOLITES OF ASPERGILLUS QUADRILINEATUS AND CONSTITUENTS OF PRIMULA DENTINCULATA AND SCHWEINFURTHIA
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Title of Thesis
CHEMICAL INVESTIGATION OF THE METABOLITES OF ASPERGILLUS QUADRILINEATUS AND CONSTITUENTS OF PRIMULA DENTINCULATA AND SCHWEINFURTHIA

Author(s)
Viqar Sultana
Institute/University/Department Details
University of Karachi, Pakistan/H.E.J. Research Institute of Chemistry
Session
1990
Subject
Chemistry
Number of Pages
180
Keywords (Extracted from title, table of contents and abstract of thesis)

Abstract
The present thesis is divided into three part. The part-1 is concerned with the chemical investigation of the metabolites of Aspergillus quadrilineatus. This has resulted in the isolation and structure elucidation of one new anthraquinone metabolite namely 7-methoxy-averufin in addition to a number of other metabolites already from other Aspergillus species, on the basis of spectral studies. 7-Methoxy averufin

The part-II of thesis deals with the studies on the chemical constituents of Schweinfurthia papilionacea. The two novel macrocyclic spermine alkaloids namely 11-epi-ephedradine A (11-epi-orantine) and schweinine were isolated along with ephedradine A (oranitine) which has already been reported from Ephedra roots, but isolated for the first time from this plant. Their structure were determined by spectral and chemical studies and the stereochemistry has been assigned on the basis of 2D-nmr techniques 1. 11-epi-ephedradine A (11-epi-orantine) 2. Schweinine

The part-III of the thesis describes the isolation of three new triterpenoid saponins namely primulanin, denticin and denticulatin from Primula denticulate Sm. (Primulaceae). One more saponin namely saxifragifolin B (deglucocyclamin I) was isolated for the first time from this plant although its occurrence in only two other plants Androsace saxifragifolia and Cyclamen europaeum has been reported earlier. The structures of all these saponins were determined through spectroscopic and chemical studies. These are as follows: 1. Primulanin (3-O-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyloxy]-16α-hydroxy-13 β,28-epoxy-olean-30-al).2. Denticin (3β-{O-β-D-glucopyranosyl-(1→4)-[O-β-D-xylopyranosyl-(1→2)]-O-β-D-glucopyranosyl-(1→4)-[ O-β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyloxy}-16α-hydroxy-13β,28-epoxy-onean-30-al) 3. Denticulatin (3β-{O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-O-β-D-xylopyranosyl-(1→4)-[O-β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyloxy}-16α-hydroxy-13β,28-epoxy-onean-30-al)

Download Full Thesis
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S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents
97.55 KB
2 1 (Part-1) Chemical investigation of the metabolites of aspergillus quadrilineatus 5
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  1.1 The genus Aspergillus 5
  1.2 Quinones of Aspergillus species 7
  1.3 Aspergillus quadrilineatus 38
  1.4 Present work 41
  1.5 Isolation and characterizatrion of sterigmatocystin 41
  1.6 Isolation characterization of 7-methoxy averufin 43
  1.7 Isolation and characterization of averufin 47
  1.8 Isolation and characterization of versicolorin B 49
  1.8 Isolation and characterization of ergosterol 51
  1.9 Isolation and characterization of ergosterol peroxide 54
  1.10 Experimental 55
  1.11 General notes 55
  1.12 Cultural conditions and characteristics 56
  1.13 Harvesting and extraction of mycelium 56
  1.14 Sterigmatocystin 58
  1.15 7-Methoxy averufin 59
  1.16 Averufin 60
  1.17 Versicolorin 3 62
  1.18 Ergosterol 64
  1.19 Ergosterol peroxide 65
  1.20 References 66
3 2 (Part-2) Studies on the Chemical constituents of schweinfurthia Papilionacea 72
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  2.1 Alkaloids 72
  2.2 The genus Schweinfurthia 74
  2.3 Present work 76
  2.4 characterization of 11-epi-Ephedradine A (11-epi-orantine) 76
  2.5 Characterizaiton of ephedradine A (Orantine) 91
  2.6 Characterization of schweinine 98
  2.7 Experimental 110
  2.8 General notes 110
  2.9 11-epi-ephedradine A (11-epi-Orantine) 113
  2.10 Ephedradine A (Orantine) 116
  2.11 Schweinine 117
  2.12 References 119
4 3 (Part-2) Introduction 121
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  3.1 Saponins 121
  3.2 The genus primula 123
  3.3 Primula denticulata 130
  3.4 Present work 134
  3.5 Isolation and structural elucidation of primulanin (3-O[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyioxy]-16α-hydroxy-3,28-epoxy-olean-30-al) 134
  3.6 Isolation and structural elucidation of Saxifragifolin B(Deglucocyclamin I)(3-O{β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl(1→2)]-α-L-arabinopyranosyioxy}-16α-hydroxy-13β,28-epoxy-olean-30-al) 143
  3.7 Isolation and structural elucidation of Denticin(3β-O{O-β-D-glucopyranosyl-(1→4)-[O-β-D-xylopyranosyl-(1→2)-]-O-β-D-glucopyranosyl(1→4)-[O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyioxy}-16α-hydroxy-13β,28-epoxy-olean-30-al) 150
  3.8 Isolation and structural elucidation of Denticulatin(3β-{O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-[-O-β-D-xylopyranosyl-(1→2)]-O-β-D-glucopyranosyl}-(1→4)-[O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyioxy}-16α-hydroxy-13β,28-epoxy-olean-30-al) 155
  3.9 Hippocratic screening 160
  3.10 Experimental 160
  3.11 General notes 163
  3.12 Primulanin 165
  3.13 Saxifragifolin B 167
  3.14 Denticin 169
  3.15 Denticulatin 171
  3.16 3-O-(β-D-glucopyranosyl)-sitosterol 174
  3.17 References 175